I am sure you know someone in your life who is an idiot – not just a standard, run-of-the-mill idiot, but a truly world-class idiot who things just magically work out for regardless of their ineptitude. Oh, did you go to class and take notes and study and take practice exams, while this person showed up hungover (when they even bothered to show up) and didn’t study at all and still swung a better grade than you? Fuck that guy. This incredibly fortunate dipshit who had everything break their way would look at Timothy Dexter and be outright insulted by his good fortunate resulting from absolutely nothing of his own doing.
Timmy Dexter was born in 1747 in Massachusetts to parents who had emigrated from Ireland; in other words, Dexter was dirt poor and poorly educated, dropping out of eight grade. Before doing anything in his own life, he had a number of strikes against him – a poor Irish-American prior to the Revolutionary War of low birth. Shockingly, this was not as inhibitory as you may have expected. Dexter worked as a leather-working apprentice in South Carolina before schmoozing his way into a wealthy Massachusetts widow’s pants who was nine years his senior with four kids. Dexter knew enough to buy when demand was low – this will be a recurring thread.
While not playing much a role during the Revolutionary War (COWARD!), he spent thousands of dollars on heretofore worthless Continental currency. Fortunately for him, Congress moved shortly after to confirm this currency as the American dollar. Suddenly, Dexter had moved from upper-middle class to exorbitantly wealthy with a blind stroke of luck. A bit of backstory here – as an uneducated Irishman, the existing upper class did not approve of this idiot crashing their parties and acting as an equal. One source cited Bostonian elites wanting to bankrupt him by turning him on to the Continental currency which they were certain had no future. Obviously, this backfired because this is the luckiest idiot in the history of the planet.
Now an extremely wealthy, as well as an extremely new member of high society, Dexter could not be as easily boxed out. This did not stop other, better-educated and more knowledgeable members of the bourgeois from fucking with him endlessly. He was pressured/tricked into shipping bedpans to the West Indies – the elites thought this was hilarious, as the West Indies were full of detestable savages who shit in the streets. Joke’s on those assholes, because bedpans were in huge demand by local high-class ladies. Dexter made a killing on this joke. In a similar vein, some other jokers told him he should sell gloves to the South Sea/Polynesia islands – the joke being they’re all poor and disgusting and would never use gloves! Hilarious! Turns out, merchants crossing the Pacific Ocean bought them en masse to turn around and sell to the Chinese, who LOVED gloves.
You read the header – you know this is only the start. A common parlance of the era was ‘shipping cats to the Indies’ for irresponsible behavior, because the Indies were overwhelmed with stray cats at the time. Spoiler – Dexter heard this and thought ‘that seems like a great idea’. This rich asshole ran around Boston alleyways collecting stray cats, which he promptly dumped onto a southbound ship and marketed as a solution to widespread rat infestation. He sold BOATLOADS of stray cats to islands already filled with cats because he was clever enough to market them as a solution to rats. I always used to shit on marketing majors, but if they have a fraction of the guile of Timothy Dexter, then the insurmountable student loan debt will be worth it.
Is three instances of dumb luck enough to prove a point? Because there’s one more, and it’s a real doozy. In keeping with the ‘saying of the time used to illustrate a fruitless action’, Dexter latched on to “shipping coal to Newcastle”. This was not just a saying at the time, but one that has persisted across generations of Brits to demonstrate the pointlessness of an action due to Newcastle’s widespread fame as a economic powerhouse solely because of it’s ability to churn out coal to supply its factors as well as factories around the rest of England AND the colonies. Newcastle turned out coal like a minor US Senator turns out female summer interns. People everywhere laughed at what a remarkable idiot he was, and were excited to watch what would certainly be his final downfall. Somewhere between the bottles of champagne being popped, but before the cheers, Newcastle coal miners went on strike. Dexter sold his coal to the coal-producing capital of the world for a premium multiple times over.
Dexter, having made a fortunate at exporting the most useless shit on the planet to corners of the world were no one wanted it until they immediately did, decided to turn his attention elsewhere. He was going to publish a book! Remember when I said he dropped out of eight grade? This book was SHIT. The book, titled “A Pickle for the Knowing Ones”, was 8,847 (mostly misspelled) words, almost entirely without punctuation and entirely random capitalization, and included divergent tirades about how much Dexter hated his local politicians and clergy, as well as his wife. Who would want to read this bullshit? EVERYONE apparently. It got eight reprintings, with one addressing the concerns of a lack of punctuation with an addendum full of nothing but commas and periods with a note that readers could distribute them as they please. It’s like the exact opposite of reading my writing.
In his newfound fame, he developed a habit of bringing mistresses to the home he shared with his wife. When his wife, understandably outraged, would scream and yell at him, he would tell his new mistress to ignore her, as it was only the ghost of his ex-wife haunting his bachelor pad. I have never been more divided over “the greatest thing I have ever heard” or “the worst thing you could do to a spouse short of OJ Simpson”. Before long, Dexter was convinced most of his friends were around only because he was wealthy, and decided to fake his death, as one does when they wish to test the loyalty of their friends. Three thousand people showed up to the fake wake, which was immediately spoiled after he stormed out of the back of the hall to cane his wife for not crying hard enough. Gee, why wouldn’t she be upset that her shit-ass husband was dead. I believe this also settles the “awesome or horrible” debacle addressed earlier.
One critic had his disgust with the entire Timothy Dexter experience quoted as. “For what purpose are riches given to some men unless to display in more glowing colours the disgusting deformities of their Characters?”, but that guy still had no idea what was coming. Did you think we were done? Can you believe someone could be even more ridiculous then everything you had already read above? Because this is Timothy Dexter we’re talking about here. Despite the American revolution successfully seceding from the British and monarchy, he anointed himself a Lord. He bought an enormous palace which he covered in statutes of great men like George Washington, Thomas Jefferson, Napoleon, Louis XVI, John Hancock, William Pitt, and, uhhh… himself. You’d think this was bold, but really these other guys were fortunate to be merely associated with a man whose placard read “I am the first in the East, the first in the West, and the greatest philosopher in the Western World”. You think you’ve seen luck go to someone’s head, but you will never make the mistake again after learning about Timothy Dexter, the man even myth couldn’t exaggerate.
Musings and Malarkey 
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